A Photochemical Entry to Depsides:  Synthesis of Gustastatin

Abstract

Herein, we propose a modular and general strategy to construct orcinol-type depsides based on the photolysis of functionalized benzodioxinones (I). Notably, resorcinylic esters are obtained without competing isocoumarin (II) formation, exemplified by the first total synthesis of gustastatin in 10 steps from commercially available trihydroxybenzoic acid. [Structure: see text]

A Ratiometric Fluorescent Probe for Biological Signaling Molecule H2S: Fast Response and High Selectivity

“…It is nevertheless surprising that 98 % of the starting 2‐(9‐bromononyl)‐3‐phenyloxirane was recovered after heating for 24 h under such conditions. The method was used by De Brabander et al for the effective isomerization of 7‐benzyloxy‐5‐(3‐pentyloxiranyl)‐2,2‐diphenylbenzo‐1,3‐dioxin‐4‐one [Equation (6)] 21 …”

Transition metals in organic synthesis: Highlights for the year 2005

“…Alkenyl tellurides were coupled with alkynyltrifluoroborates [265]. Coupling of alkyl borates were used in synthesis of EI-1941-1 and EI-1941-2 [58], of alkenylborate in synthesis of gustastatin [266], toward (+)-sorangicin [267], serofendic acids A and B [268] and C6-C21 segment of amphidinolide E [269] and of an alkynylborate in a synthesis of latrunculin A [108].…”

“…(266) and (267)) [1343]. Ruthenium catalyzed a cycloisomerization of 1,3-diene-5-ynes having an adjacent methylene group to form substituted benzenes (Eq.…”

Pd‐Mediated Reactions of Epoxides

“…The method was used by De Brabander et al for the effective isomerization of 7-benzyloxy-5-(3-pentyloxiranyl)-2,2-diphenylbenzo-1,3-dioxin-4-one [Equation (6)]. [21] With the Pd(OAc) 2 /PPh 3 system, Kulasegaram and Kulawiec achieved selective isomerization of the aryl-substituted epoxy group in 1-phenyl-1,2,11,12-diepoxydodecane [Equation (7)]. [9] …”